4-Vinylpyridine

4-Vinylpyridine
Names
	Preferred IUPAC name 4-Ethenylpyridine
	Other names 4-VP
Identifiers
CAS Number	100-43-6;
3D model (JSmol)	Interactive image;
Beilstein Reference	104506
ChemSpider	7221;
ECHA InfoCard	100.002.593
EC Number	202-852-0;
PubChem CID	7502;
UNII	I56G67XM8D;
CompTox Dashboard (EPA)	DTXSID0051499 ;
	InChI InChI=1S/C7H7N/c1-2-7-3-5-8-6-4-7/h2-6H,1H2 Key: KFDVPJUYSDEJTH-UHFFFAOYSA-N;
	SMILES C=CC1=CC=NC=C1;
Properties
Chemical formula	C7H7N
Molar mass	105.140 g·mol−1
Appearance	colorless liquid
Density	0.988 g/cm3
Boiling point	62–65 °C (144–149 °F; 335–338 K) 15 mmHg
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H226, H301, H314, H315, H317, H319, H330, H334, H411
Precautionary statements	P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P272, P273, P280, P284, P285, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P304+P341, P305+P351+P338, P310, P320, P321, P330, P332+P313, P333+P313, P337+P313, P342+P311, P362, P363, P370+P378, P391, P403+P233, P403+P235, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

4-Vinylpyridine (4-VP) is an organic compound with the formula CH₂CHC₅H₄N. It is a derivative of pyridine with a vinyl group in the 4-position. It is a colorless liquid, although impure samples are often brown. It is a monomeric precursor to specialty polymers. 4-Vinylpyridine is prepared by the condensation of 4-methylpyridine and formaldehyde.^[1]

4-VP is sometimes used in biochemistry to alkylate protein cysteine residues. When compared to other alkylation agents, such as iodoacetamide, acrylamide, and N-ethylmaleimide, 4-VP is less reactive, meaning the completion rate of cysteine alkylation is lower, but it also yields fewer side reactions.^[2] For some uses, such as during mass spectrometry measurements, 4-VP might be better because it is basic and can thus be protonated, adding net charge.^[3]

References

^ Shimizu, Shinkichi; Watanabe, Nanao; Kataoka, Toshiaki; Shoji, Takayuki; Abe, Nobuyuki; Morishita, Sinji; Ichimura, Hisao (2007). "Pyridine and Pyridine Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_399. ISBN 978-3527306732.
^ Suttapitugsakul, Suttipong; Xiao, Haopeng; Smeekens, Johanna; Wu, Ronghu (2017). "Evaluation and optimization of reduction and alkylation methods to maximize peptide identification with MS-based proteomics". Molecular BioSystems. 13 (12): 2574–2582. doi:10.1039/C7MB00393E. ISSN 1742-206X. PMC 5698164. PMID 29019370.
^ Sechi, Salvatore; Chait, Brian T. (1998-12-01). "Modification of Cysteine Residues by Alkylation. A Tool in Peptide Mapping and Protein Identification". Analytical Chemistry. 70 (24): 5150–5158. doi:10.1021/ac9806005. ISSN 0003-2700. PMID 9868912.

[Ullmann-1] Shimizu, Shinkichi; Watanabe, Nanao; Kataoka, Toshiaki; Shoji, Takayuki; Abe, Nobuyuki; Morishita, Sinji; Ichimura, Hisao (2007). "Pyridine and Pyridine Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_399. ISBN 978-3527306732.

[2] Suttapitugsakul, Suttipong; Xiao, Haopeng; Smeekens, Johanna; Wu, Ronghu (2017). "Evaluation and optimization of reduction and alkylation methods to maximize peptide identification with MS-based proteomics". Molecular BioSystems. 13 (12): 2574–2582. doi:10.1039/C7MB00393E. ISSN 1742-206X. PMC 5698164. PMID 29019370.

[3] Sechi, Salvatore; Chait, Brian T. (1998-12-01). "Modification of Cysteine Residues by Alkylation. A Tool in Peptide Mapping and Protein Identification". Analytical Chemistry. 70 (24): 5150–5158. doi:10.1021/ac9806005. ISSN 0003-2700. PMID 9868912.

[1]

[2]

[3]

See also

References